Diisopropylamine → 2-Acetyl-4-(4-pyridyl)cyclohexanone

HRID 621708Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[N:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.[C:26](C1NC=CN=1)(=[O:28])[CH3:27]>O1CCCC1.CCCCCC>[C:26]([CH:21]1[CH2:20][CH:19]([C:16]2[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=2)[CH2:24][CH2:23][C:22]1=[O:25])(=[O:28])[CH3:27]

Participants

Conditions

Temperature: -78 °C

Procedure

3.2 ml of diisopropylamine was dissolved in 40 ml of tetrahydrofuran and 14.2 ml of a 1.6 M solution of n-butyllithium in hexane was added thereto at -20° C. A solution prepared by dissolving 2 g of 4-(4-pyridyl)cyclohexanone in 40 ml of tetrahydrofuran was further added thereto at -40° C. The obtained reaction mixture was cooled to -78° C. and 2.5 g of acetylimidazole dissolved in 40 ml of tetrahydrofuran was added thereto. After stirring at room temperature, the reaction mixture was poured onto ice water and washed with ether. The aqueous phase was saturated with ammonium chloride and extracted with methylene chloride to give 1.65 g of 2-acetyl-4-(4-pyridyl)cyclohexanone. NMRδTMSCDCl3 : 1.7-2.2 (3H, m), 2.16 (3H, s), 2.3-2.6 (3H, m), 2.6-2.9 (1H, m), 7.10 (2H, dd), 8.55 (2H, dd) and 15.7 (1H, s).

Workup

customat -20° C
customA solution prepared
additionwas further added
customat -40° C
customThe obtained reaction mixture
additionwas added
additionthe reaction mixture was poured onto ice water
washwashed with ether
extractionextracted with methylene chloride

Sources & evidence

ORD record: ord-3d3831fbb2054052aef941f608a32fb5
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04824952

Reaction notes

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